Origins of initiation rate differences in ruthenium olefin metathesis catalysts containing chelating benzylidenes

Journal of the American Chemical Society

Volumn 137, Issue 17, 2015, Pages 5782-5792

  Engle, Keary M ^a   Lu, Gang ^b   Luo, Shao Xiong ^a   Henling, Lawrence M ^a   Takase, Michael K ^a   Liu, Peng ^b,c   Houk, K N ^c   Grubbs, Robert H ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOND LENGTH; BOND STRENGTH (CHEMICAL); BOND STRENGTH (MATERIALS); CATALYSTS; CHELATION; CRYSTALLOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; REACTION KINETICS; RUTHENIUM;

BENZYLIDENE; DFT CALCULATION; ENERGY MINIMIZED STRUCTURES; INITIATION RATE; OLEFIN METATHESIS; SECOND GENERATION; THERMODYNAMIC PARAMETER; X RAY CRYSTAL STRUCTURES;

X RAY CRYSTALLOGRAPHY;

ALKENE; BENZYLIDENE DERIVATIVE; RUTHENIUM; CHELATING AGENT; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYST; CHELATION; CHEMICAL BOND; CHEMICAL REACTION; CONCEPTUAL FRAMEWORK; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFIN METATHESIS; RING CLOSING METATHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; QUANTUM THEORY; SYNTHESIS;

ALKENES; BENZYLIDENE COMPOUNDS; CATALYSIS; CHELATING AGENTS; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; QUANTUM THEORY; RUTHENIUM; THERMODYNAMICS;

EID: 84928969245     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b01144     Document Type: Article

References (91)

1. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29
2. Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043
3. Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633
4. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527
5. Schrock, R. R. Chem. Rev. 2009, 109, 3211-3226
6. Samojowicz, C.; Bieniek, M.; Grela, K. Chem. Rev. 2009, 109, 3708-3742
7. Vougioukalakis, G. C.; Grubbs, R. H. Chem. Rev. 2010, 110, 1746-1787
8. Hoveyda, A. H. J. Org. Chem. 2014, 79, 4763-4792
9. Nelson, D. J.; Manzini, S.; Urbina-Blanco, C. A.; Nolan, S. P. Chem. Commun. 2014, 50, 10355-10375
10. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974-3975
11. Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859
12. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041
13. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110
14. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956
15. Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799
16. Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23
17. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179
18. Gessler, S.; Randl, S.; Blechert, S. Tetrahedron Lett. 2000, 41, 9973-9976
19. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554
20. For a review of ruthenium olefin metathesis catalysts containing chelating benzylidenes, see: Vidavsky, Y.; Anaby, A.; Lemcoff, N. G. Dalton Trans. 2012, 41, 32-43
21. Shu, C.; Zeng, X.; Hao, M.-H.; Wei, X.; Yee, N. K.; Busacca, C. A.; Han, Z.; Farina, V.; Senanayake, C. H. Org. Lett. 2008, 10, 1303-1306
22. Farina, V.; Shu, C.; Zeng, X.; Wei, X.; Han, Z.; Yee, N. K.; Senanayake, C. H. Org. Process Res. Dev. 2009, 13, 250-254
23. Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 794-796
24. Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403-2405
25. Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502-12508
26. Berlin, J. M.; Campbell, K.; Ritter, T.; Funk, T. W.; Chlenov, A.; Grubbs, R. H. Org. Lett. 2007, 9, 1339-1342
27. Gatti, M.; Vieille-Petit, L.; Luan, X.; Mariz, R.; Drinkel, E.; Linden, A.; Dorta, R. J. Am. Chem. Soc. 2009, 131, 9498-9499
28. Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038-4040
29. Zaja, M.; Connon, S. J.; Dunne, A. M.; Rivard, M.; Buschmann, N.; Jiricek, J.; Blechert, S. Tetrahedron 2003, 59, 6545-6558
30. Zhan, Z.-Y. J. Recyclable Ruthenium Catalysts for Metathesis Reactions. U.S. Patent US20070043180 A1, Feb 22, 2007.
31. Vinokurov, N.; Garabatos-Perera, J. R.; Zhao-Karger, Z.; Wiebcke, M.; Butenschön, H. Organometallics 2008, 27, 1878-1886
32. Rix, D.; Caijo, F.; Laurent, I.; Boeda, F.; Clavier, H.; Nolan, S. P.; Mauduit, M. J. Org. Chem. 2008, 73, 4225-4228
33. Thiel, V.; Hendann, M.; Wannowius, K.-J.; Plenio, H. J. Am. Chem. Soc. 2012, 134, 1104-1114
34. Kos, P.; Savka, R.; Plenio, H. Adv. Synth. Catal. 2013, 355, 439-447
35. Nelson, D. J.; Queval, P.; Rouen, M.; Magrez, M.; Toupet, L.; Caijo, F.; Borré, E.; Laurent, I.; Crévisy, C.; Baslé, O.; Mauduit, M.; Percy, J. M. ACS Catal. 2013, 3, 259-264
36. van der Schaaf, P. A.; Kolly, R.; Kirner, H.-J.; Rime, F.; Mühlebach, A.; Hafner, A. J. Organomet. Chem. 2000, 606, 65-74
37. Fürstner, A.; Thiel, O. R.; Lehmann, C. W. Organometallics 2002, 21, 331-335
38. Slugovc, C.; Perner, B.; Stelzer, F.; Mereiter, K. Organometallics 2004, 23, 3622-3626
39. Barbasiewicz, M.; Szadkowska, A.; Bujok, R.; Grela, K. Organometallics 2006, 25, 3599-3604
40. Hejl, A.; Day, M. W.; Grubbs, R. H. Organometallics 2006, 25, 6149-6154
41. Ben-Asuly, A.; Tzur, E.; Diesendruck, C. E.; Sigalov, M.; Goldberg, I.; Lemcoff, N. G. Organometallics 2008, 27, 811-813
42. Kost, T.; Sigalov, M.; Goldberg, I.; Ben-Asuly, A.; Lemcoff, N. G. J. Organomet. Chem. 2008, 693, 2200-2203
43. Tzur, E.; Szadkowska, A.; Ben-Asuly, A.; Makal, A.; Goldberg, I.; Woźniak, K.; Grela, K.; Lemcoff, N. G. Chem.-Eur. J. 2010, 16, 8726-8737
44. Szadkowska, A.; Żukowska, K.; Pazio, A. E.; Woźniak, K.; Kadyrov, R.; Grela, K. Organometallics 2011, 30, 1130-1138
45. Ginzburg, Y.; Anaby, A.; Vidavsky, Y.; Diesendruck, C. E.; Ben-Asuly, A.; Goldberg, I.; Lemcoff, N. G. Organometallics 2011, 30, 3430-3437
46. Lexer, C.; Burtscher, D.; Perner, B.; Tzur, E.; Lemcoff, N. G.; Slugovc, C. J. Organomet. Chem. 2011, 696, 2466-2470
47. Peeck, L. H.; Savka, R. D.; Plenio, H. Chem.-Eur. J. 2012, 18, 12845-12853
48. Barbasiewicz, M.; Michalak, M.; Grela, K. Chem.-Eur. J. 2012, 18, 14237-14241
49. Barbasiewicz, M.; Bieniek, M.; Michrowska, A.; Szadkowska, A.; Makal, A.; Woźniak, K.; Grela, K. Adv. Synth. Catal. 2007, 349, 193-203
50. Hejl, A. Ph.D. Thesis, California Institute of Technology, Pasadena, CA, 2007.
51. Bornand, M.; Torker, S.; Chen, P. Organometallics 2007, 26, 3585-3596
52. Bieniek, M.; Bujok, R.; Cabaj, M.; Lugan, N.; Lavigne, G.; Arlt, D.; Grela, K. J. Am. Chem. Soc. 2006, 128, 13652-13653
53. Bieniek, M.; Samojowicz, C.; Sashuk, V.; Bujok, R.; ͆ledź, P.; Lugan, N.; Lavigne, G.; Arlt, D.; Grela, K. Organometallics 2011, 30, 4144-4158
54. Vougioukalakis, G. C.; Grubbs, R. H. Chem.-Eur. J. 2008, 14, 7545-7556
55. Solans-Monfort, X.; Pleixats, R.; Sodupe, M. Chem.-Eur. J. 2010, 16, 7331-7343
56. Vorfalt, T.; Wannowius, K.-J.; Plenio, H. Angew. Chem., Int. Ed. 2010, 49, 5533-5536
57. Ashworth, I. W.; Hillier, I. H.; Nelson, D. J.; Percy, J. M.; Vincent, M. A. Chem. Commun. 2011, 47, 5428-5430
58. Nuñez-Zarur, F.; Solans-Monfort, X.; Rodríguez-Santiago, L.; Sodupe, M. Organometallics 2012, 31, 4203-4215
59. Ashworth, I. W.; Hillier, I. H.; Nelson, D. J.; Percy, J. M.; Vincent, M. A. ACS Catal. 2013, 3, 1929-1939
60. Engle, K. M.; Luo, S.-X.; Grubbs, R. H. J. Org. Chem. 2015, 80, 4213-4220
61. Cote, B.; Ducharme, Y.; Frenette, R.; Friesen, R.; Martins, E. (Merck & Co.). Tri-aryl-substituted-ethane PDE4 Inhibitors. U.S. Patent US20020156105 A1, Oct 24, 2002.
62. Cherian, J.; Choi, I.; Nayyar, A.; Manjunatha, U. H.; Mukherjee, T.; Lee, Y. S.; Boshoff, H. I.; Singh, R.; Ha, Y. H.; Goodwin, M.; Lakshminarayana, S. B.; Niyomrattanakit, P.; Jiricek, J.; Ravindran, S.; Dick, T.; Keller, T. H.; Dartois, V.; Barry, C. E., III J. Med. Chem. 2011, 54, 5639-5659
63. Monsaert, S. F.; Verpoort, F. W. C. (Umicore AG & Co. KG and Ghent University). Process for Preparation of Ruthenium-Based Carbene Catalysts with Chelating Alkylidene Ligands. World Patent WO2011091980 A1, Aug 4, 2011.
64. Monsaert, S.; Drozdzak, R.; Dragutan, V.; Dragutan, I.; Verpoort, F. Eur. J. Inorg. Chem. 2008, 432-440
65. Urbina-Blanco, C. A.; Manzini, S.; Gomes, J. P.; Doppiu, A.; Nolan, S. P. Chem. Commun. 2011, 47, 5022-5024
66. Boeda, F.; Clavier, H.; Nolan, S. P. Chem. Commun. 2008, 2726-2740
67. RCM kinetics experiments were performed according to a previously published procedure. See: Ritter, T.; Hejl, A.; Wenzel, A. G.; Funk, T. W.; Grubbs, R. H. Organometallics 2006, 25, 5740-5745
68. CCDC 1017843 (5), 1044211 (9), 1044212 (10), 1017842 (11), and 1017841 (12) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
69. Barbasiewicz, M.; Szadkowska, A.; Makal, A.; Jarzembska, K.; Woźniak, K.; Grela, K. Chem.-Eur. J. 2008, 14, 9330-9337
70. All of the computations were performed in the gas phase with Gaussian 09: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
71. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
72. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
73. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
74. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824
75. Poater, A.; Pump, E.; Vummaleti, S. V. C.; Cavallo, L. J. Chem. Theory Comput. 2014, 10, 4442-4448
76. Adlhart, C.; Chen, P. Angew. Chem., Int. Ed. 2002, 41, 4484-4487
77. Diesendruck, C. E.; Tzur, E.; Ben-Asuly, A.; Goldberg, I.; Straub, B. F.; Lemcoff, N. G. Inorg. Chem. 2009, 48, 10819-10825
78. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
79. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101
80. Chai, J.-D.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615-6620
81. Kulkarni, A. D.; Truhlar, D. G. J. Chem. Theory Comput. 2011, 7, 2325-2332
82. Minenkov, Y.; Singstad, Å.; Occhipinti, G.; Jensen, V. R. Dalton Trans. 2012, 41, 5526-5541
83. Süßner, M.; Plenio, H. Chem. Commun. 2005, 5417-5419
84. Leuthäußer, S.; Schmidts, V.; Thiele, C. M.; Plenio, H. Chem.-Eur. J. 2008, 14, 5465-5481
85. Credendino, R.; Falivene, L.; Cavallo, L. J. Am. Chem. Soc. 2012, 134, 8127-8135
86. Vehlow, K.; Maechling, S.; Blechert, S. Organometallics 2006, 25, 25-28
87. Vehlow, K.; Maechling, S.; Köhler, K.; Blechert, S. J. Organomet. Chem. 2006, 691, 5267-5277
88. Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848-10849
89. Green, A. G.; Liu, P.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 4575-4583
90. Fernández, I.; Bickelhaupt, F. M.; Cossío, F. P. Chem.-Eur. J. 2012, 18, 12395-12403
91. Fernández, I.; Bickelhaupt, F. M.; Cossío, F. P. Chem.-Eur. J. 2014, 20, 10791-10801